4. The Departed

2006

Martin Scorsese won his first Oscar for Best Achievement in Directing for his efforts on The Departed. Many said he deserved it much earlier, and while that may be the case, he certainly merited such recognition for this film. A loose remake of the Hong Kong movie Infernal Affairs, The Departed follows two South Boston cops working undercover on opposite sides of the law. DiCaprio plays a good cop working undercover in the Irish mafia, while Matt Damon plays a bad cop working as a mole for the Irish mafia. The story follows their attempts to root each other out.

A cast supported by Leonardo DiCaprio, Matt Damon, Martin Sheen, Alec Baldwin, and Mark Wahlberg was enough to draw people in, and their strong performances kept them coming back. The other big reason for The Departed's success? Jack. Back with a vengeance as a South Boston crime lord, Jack Nicholson assumed the role of evil incarnate. Whether he was snorting mountains of coke, spitting racist comments or spitting on himself, Jack tipped the scales to make Martin Scorsese’s picture a heavyweight.